Several changes:

1) Add an option to specify the time format when sending to device. This is the analog of the same option that already exists for save to disk.
2) refactor the format_field code. Remove the special parameters on format_field. Add format_field_extended that returns a 4-element tuple (name, formatted val, original val, field metadata).
3) change (simplify) usbms collections management to use new format_field_extended method.
4) change device.py to not call sync_booklists twice.
5) add the fix for gui-not-updating, in hopes that we can avoid merge conflicts

src/calibre/devices/usbms/books.py

@@ -94,12 +94,12 @@ class CollectionsBookList(BookList):
     def supports_collections(self):
         return True
 
-    def compute_category_name(self, attr, category, cust_field_meta):
+    def compute_category_name(self, attr, category, field_meta):
         renames = tweaks['sony_collection_renaming_rules']
         attr_name = renames.get(attr, None)
         if attr_name is None:
-            if attr in cust_field_meta:
+            if field_meta['is_custom']:
-                attr_name = '(%s)'%cust_field_meta[attr]['name']
+                attr_name = '(%s)'%field_meta['name']
             else:
                 attr_name = ''
         elif attr_name != '':
@@ -138,23 +138,23 @@ class CollectionsBookList(BookList):
                 # specified 'on_connect'
                 attrs = collection_attributes
             meta_vals = book.get_all_non_none_attributes()
-            cust_field_meta = book.get_all_user_metadata(make_copy=False)
             for attr in attrs:
                 attr = attr.strip()
-                ign, val = book.format_field(attr,
+                ign, val, orig_val, fm = book.format_field_extended(attr)
-                                             ignore_series_index=True,
-                                             return_multiples_as_list=True)
                 if not val: continue
                 if isbytestring(val):
                     val = val.decode(preferred_encoding, 'replace')
                 if isinstance(val, (list, tuple)):
                     val = list(val)
+                elif fm['datatype'] == 'series':
+                    val = [orig_val]
+                elif fm['datatype'] == 'text' and fm['is_multiple']:
+                    val = orig_val
                 else:
                     val = [val]
                 for category in val:
                     is_series = False
-                    if attr in cust_field_meta: # is a custom field
+                    if fm['is_custom']: # is a custom field
-                        fm = cust_field_meta[attr]
                         if fm['datatype'] == 'text' and len(category) > 1 and \
                                 category[0] == '[' and category[-1] == ']':
                             continue
@@ -168,8 +168,7 @@ class CollectionsBookList(BookList):
                                 ('series' in collection_attributes and
                                  meta_vals.get('series', None) == category):
                             is_series = True
-                    cat_name = self.compute_category_name(attr, category,
+                    cat_name = self.compute_category_name(attr, category, fm)
-                                                          cust_field_meta)
                     if cat_name not in collections:
                         collections[cat_name] = []
                         collections_lpaths[cat_name] = set()

src/calibre/devices/usbms/device.py

@@ -829,12 +829,14 @@ class Device(DeviceConfig, DevicePlugin):
         ext = os.path.splitext(fname)[1]
 
         from calibre.library.save_to_disk import get_components
+        from calibre.library.save_to_disk import config
+        opts = config().parse()
         if not isinstance(template, unicode):
             template = template.decode('utf-8')
         app_id = str(getattr(mdata, 'application_id', ''))
         # The db id will be in the created filename
         extra_components = get_components(template, mdata, fname,
-                length=250-len(app_id)-1)
+                timefmt=opts.send_timefmt, length=250-len(app_id)-1)
         if not extra_components:
             extra_components.append(sanitize(self.filename_callback(fname,
                 mdata)))

src/calibre/ebooks/metadata/book/base.py

@@ -343,8 +343,11 @@ class Metadata(object):
     def format_rating(self):
         return unicode(self.rating)
 
-    def format_field(self, key, ignore_series_index=False,
+    def format_field(self, key):
-                     return_multiples_as_list=False):
+        name, val, ign, ign = self.format_field_extended(key)
+        return (name, val)
+
+    def format_field_extended(self, key):
         from calibre.ebooks.metadata import authors_to_string
         '''
         returns the tuple (field_name, formatted_value)
@@ -352,43 +355,41 @@ class Metadata(object):
         if key in self.user_metadata_keys:
             res = self.get(key, None)
             if res is None or res == '':
-                return (None, None)
+                return (None, None, None, None)
+            orig_res = res
             cmeta = self.get_user_metadata(key, make_copy=False)
             name = unicode(cmeta['name'])
             datatype = cmeta['datatype']
             if datatype == 'text' and cmeta['is_multiple']:
-                if not return_multiples_as_list:
                 res = u', '.join(res)
             elif datatype == 'series':
-                if not ignore_series_index:
                 res = res + \
                    ' [%s]'%self.format_series_index(val=self.get_extra(key))
             elif datatype == 'datetime':
                 res = format_date(res, cmeta['display'].get('date_format','dd MMM yyyy'))
             elif datatype == 'bool':
                 res = _('Yes') if res else _('No')
-            return (name, res)
+            return (name, res, orig_res, cmeta)
 
         if key in field_metadata and field_metadata[key]['kind'] == 'field':
             res = self.get(key, None)
             if res is None or res == '':
-                return (None, None)
+                return (None, None, None, None)
+            orig_res = res
             fmeta = field_metadata[key]
             name = unicode(fmeta['name'])
             datatype = fmeta['datatype']
             if key == 'authors':
                 res = authors_to_string(res)
             elif datatype == 'text' and fmeta['is_multiple']:
-                if not return_multiples_as_list:
                 res = u', '.join(res)
             elif datatype == 'series':
-                if not ignore_series_index:
                 res = res + ' [%s]'%self.format_series_index()
             elif datatype == 'datetime':
                 res = format_date(res, fmeta['display'].get('date_format','dd MMM yyyy'))
-            return (name, res)
+            return (name, res, orig_res, fmeta)
 
-        return (None, None)
+        return (None, None, None, None)
 
     def __unicode__(self):
         from calibre.ebooks.metadata import authors_to_string

src/calibre/gui2/actions/add.py

@@ -230,7 +230,7 @@ class AddAction(InterfaceAction):
         self._files_added(paths, names, infos, on_card=on_card)
         # set the in-library flags, and as a consequence send the library's
         # metadata for this book to the device. This sets the uuid to the
-        # correct value.
+        # correct value. Note that set_books_in_library might sync_booklists
         self.gui.set_books_in_library(booklists=[model.db], reset=True)
         model.reset()
 

src/calibre/gui2/device.py

@@ -745,6 +745,7 @@ class DeviceMixin(object): # {{{
         if job.failed:
             self.device_job_exception(job)
             return
+        # set_books_in_library might schedule a sync_booklists job
         self.set_books_in_library(job.result, reset=True)
         mainlist, cardalist, cardblist = job.result
         self.memory_view.set_database(mainlist)
@@ -789,11 +790,12 @@ class DeviceMixin(object): # {{{
             self.device_manager.remove_books_from_metadata(paths,
                     self.booklists())
             model.paths_deleted(paths)
-            self.upload_booklists()
         # Force recomputation the library's ondevice info. We need to call
         # set_books_in_library even though books were not added because
-        # the deleted book might have been an exact match.
+        # the deleted book might have been an exact match. Upload the booklists
-        self.set_books_in_library(self.booklists(), reset=True)
+        # if set_books_in_library did not.
+        if not self.set_books_in_library(self.booklists(), reset=True):
+            self.upload_booklists()
         self.book_on_device(None, None, reset=True)
         # We need to reset the ondevice flags in the library. Use a big hammer,
         # so we don't need to worry about whether some succeeded or not.
@@ -1280,8 +1282,6 @@ class DeviceMixin(object): # {{{
         self.device_manager.add_books_to_metadata(job.result,
                 metadata, self.booklists())
 
-        self.upload_booklists()
-
         books_to_be_deleted = []
         if memory and memory[1]:
             books_to_be_deleted = memory[1]
@@ -1291,12 +1291,15 @@ class DeviceMixin(object): # {{{
         # book already there with a different book. This happens frequently in
         # news. When this happens, the book match indication will be wrong
         # because the UUID changed. Force both the device and the library view
-        # to refresh the flags.
+        # to refresh the flags. Set_books_in_library could upload the booklists.
-        self.set_books_in_library(self.booklists(), reset=True)
+        # If it does not, then do it here.
+        if not self.set_books_in_library(self.booklists(), reset=True):
+            self.upload_booklists()
         self.book_on_device(None, reset=True)
         self.refresh_ondevice_info(device_connected = True)
 
-        view = self.card_a_view if on_card == 'carda' else self.card_b_view if on_card == 'cardb' else self.memory_view
+        view = self.card_a_view if on_card == 'carda' else \
+            self.card_b_view if on_card == 'cardb' else self.memory_view
         view.model().resort(reset=False)
         view.model().research()
         for f in files:
@@ -1371,7 +1374,7 @@ class DeviceMixin(object): # {{{
             try:
                 db = self.library_view.model().db
             except:
-                return
+                return False
             # Build a cache (map) of the library, so the search isn't On**2
             self.db_book_title_cache = {}
             self.db_book_uuid_cache = {}
@@ -1466,10 +1469,13 @@ class DeviceMixin(object): # {{{
                 # Set author_sort if it isn't already
                 asort = getattr(book, 'author_sort', None)
                 if not asort and book.authors:
-                    book.author_sort = self.library_view.model().db.author_sort_from_authors(book.authors)
+                    book.author_sort = self.library_view.model().db.\
+                                author_sort_from_authors(book.authors)
 
         if update_metadata:
             if self.device_manager.is_device_connected:
-                self.device_manager.sync_booklists(None, booklists)
+                self.device_manager.sync_booklists(
+                                    Dispatcher(self.metadata_synced), booklists)
+        return update_metadata
     # }}}
 

src/calibre/gui2/preferences/sending.py

@@ -22,6 +22,9 @@ class ConfigWidget(ConfigWidgetBase, Ui_Form):
 
         r = self.register
 
+        for x in ('send_timefmt',):
+            r(x, self.proxy)
+
         choices = [(_('Manual management'), 'manual'),
                 (_('Only on send'), 'on_send'),
                 (_('Automatic management'), 'on_connect')]

src/calibre/gui2/preferences/sending.ui

@@ -80,7 +80,20 @@
      </property>
     </widget>
    </item>
-   <item row="2" column="0" colspan="3">
+   <item row="2" column="0">
+    <widget class="QLabel" name="label_2">
+     <property name="text">
+      <string>Format &amp;dates as:</string>
+     </property>
+     <property name="buddy">
+      <cstring>opt_send_timefmt</cstring>
+     </property>
+    </widget>
+   </item>
+   <item row="2" column="1">
+    <widget class="QLineEdit" name="opt_send_timefmt"/>
+   </item>
+   <item row="3" column="0" colspan="3">
     <widget class="QLabel" name="label_43">
      <property name="text">
       <string>Here you can control how calibre will save your books when you click the Send to Device button. This setting can be overriden for individual devices by customizing the device interface plugins in Preferences-&gt;Advanced-&gt;Plugins</string>

src/calibre/library/save_to_disk.py

@@ -84,6 +84,9 @@ def config(defaults=None):
     x('timefmt', default='%b, %Y',
             help=_('The format in which to display dates. %d - day, %b - month, '
                 '%Y - year. Default is: %b, %Y'))
+    x('send_timefmt', default='%b, %Y',
+            help=_('The format in which to display dates. %d - day, %b - month, '
+                '%Y - year. Default is: %b, %Y'))
     x('to_lowercase', default=False,
             help=_('Convert paths to lowercase.'))
     x('replace_whitespace', default=False,